CA2421040C - Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives - Google Patents

Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives Download PDF

Info

Publication number
CA2421040C
CA2421040C CA002421040A CA2421040A CA2421040C CA 2421040 C CA2421040 C CA 2421040C CA 002421040 A CA002421040 A CA 002421040A CA 2421040 A CA2421040 A CA 2421040A CA 2421040 C CA2421040 C CA 2421040C
Authority
CA
Canada
Prior art keywords
moiety
nucleoside
tert
deoxy
product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA002421040A
Other languages
English (en)
French (fr)
Other versions
CA2421040A1 (en
Inventor
Leonid Beigelman
Alexander Karpeisky
Vladimir Serebryany
Peter Haeberli
David Sweedler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sirna Therapeutics Inc
Original Assignee
Sirna Therapeutics Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sirna Therapeutics Inc filed Critical Sirna Therapeutics Inc
Publication of CA2421040A1 publication Critical patent/CA2421040A1/en
Application granted granted Critical
Publication of CA2421040C publication Critical patent/CA2421040C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • C07H11/04—Phosphates; Phosphites; Polyphosphates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
CA002421040A 2000-09-01 2001-08-31 Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives Expired - Fee Related CA2421040C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US23005700P 2000-09-01 2000-09-01
US60/230,057 2000-09-01
US28657101P 2001-04-25 2001-04-25
US60/286,571 2001-04-25
PCT/US2001/027116 WO2002018405A2 (en) 2000-09-01 2001-08-31 Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

Publications (2)

Publication Number Publication Date
CA2421040A1 CA2421040A1 (en) 2002-03-07
CA2421040C true CA2421040C (en) 2010-01-12

Family

ID=26923871

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002421040A Expired - Fee Related CA2421040C (en) 2000-09-01 2001-08-31 Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

Country Status (8)

Country Link
US (1) US6686463B2 (ja)
EP (1) EP1313752B1 (ja)
JP (1) JP2004522695A (ja)
AT (1) ATE506372T1 (ja)
AU (2) AU2001286959B2 (ja)
CA (1) CA2421040C (ja)
DE (1) DE60144479D1 (ja)
WO (1) WO2002018405A2 (ja)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY164523A (en) 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
EP1736478B1 (en) 2000-05-26 2015-07-22 IDENIX Pharmaceuticals, Inc. Methods and compositions for treating flaviviruses and pestiviruses
US7608600B2 (en) 2002-06-28 2009-10-27 Idenix Pharmaceuticals, Inc. Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
US20050136437A1 (en) * 2003-08-25 2005-06-23 Nastech Pharmaceutical Company Inc. Nanoparticles for delivery of nucleic acids and stable double-stranded RNA
WO2005078848A2 (en) * 2004-02-11 2005-08-25 University Of Tennessee Research Foundation Inhibition of tumor growth and invasion by anti-matrix metalloproteinase dnazymes
CA2561741C (en) * 2004-04-05 2016-09-27 Alnylam Pharmaceuticals, Inc. Processes and reagents for oligonucleotide synthesis and purification
JP4584986B2 (ja) * 2004-04-27 2010-11-24 アルニラム ファーマスーティカルズ インコーポレイテッド ２−アリールプロピル部分を含む１本鎖及び２本鎖オリゴヌクレオチド
AU2005323437B2 (en) * 2004-04-30 2011-10-06 Alnylam Pharmaceuticals, Inc. Oligonucleotides comprising a C5-modified pyrimidine
US7615618B2 (en) 2004-06-30 2009-11-10 Alnylam Pharmaceuticals, Inc. Oligonucleotides comprising a non-phosphate backbone linkage
US7579451B2 (en) * 2004-07-21 2009-08-25 Alnylam Pharmaceuticals, Inc. Oligonucleotides comprising a modified or non-natural nucleobase
AU2005330637B2 (en) 2004-08-04 2012-09-20 Alnylam Pharmaceuticals, Inc. Oligonucleotides comprising a ligand tethered to a modified or non-natural nucleobase
US8658608B2 (en) * 2005-11-23 2014-02-25 Yale University Modified triple-helix forming oligonucleotides for targeted mutagenesis
US8420613B2 (en) 2006-11-15 2013-04-16 The J. David Gladstone Institutes Methods and compositions for reducing amyloid beta levels
US20100172882A1 (en) * 2007-01-11 2010-07-08 Glazer Peter M Compositions and methods for targeted inactivation of hiv cell surface receptors
CA2680600A1 (en) * 2007-03-12 2008-09-18 Antigen Express, Inc. Li-rnai involved li suppression in cancer immunotherapy
WO2010039801A2 (en) 2008-10-02 2010-04-08 The J. David Gladstone Institutes Methods of treating hepatitis c virus infection
WO2010096201A2 (en) * 2009-02-22 2010-08-26 Chemgenes Corporation Synthesis of ara-2'-o-methyl-nucleosides, corresponding phosphoramidites and oligonucleotides incorporating novel modifications for biological application in therapeutics, diagnostics, g- tetrad forming oligonucleotides and aptamers
WO2010107952A2 (en) 2009-03-19 2010-09-23 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF CONNECTIVE TISSUE GROWTH FACTOR (CTGF) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
EP2408458A1 (en) 2009-03-19 2012-01-25 Merck Sharp&Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF SIGNAL TRANSDUCER AND ACTIVATOR OF TRANSCRIPTION 6 (STAT6) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
WO2010107957A2 (en) 2009-03-19 2010-09-23 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF GATA BINDING PROTEIN 3 (GATA3) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
CN102439151A (zh) 2009-03-19 2012-05-02 默沙东公司 使用短干扰核酸（siNA）的RNA干扰介导的BTB和CNC同系物1，碱性亮氨酸拉链转录因子1（Bach1）基因表达的抑制
US20120022142A1 (en) 2009-03-27 2012-01-26 Merck Sharp & Dohme Corp. RNA Interference Mediated Inhibition of Signal Transducer and Activator of Transcription 1 (STAT1) Gene Expression Using Short Interfering Nucleic Acid (siNA)
JP2012521765A (ja) 2009-03-27 2012-09-20 メルク・シャープ・エンド・ドーム・コーポレイション 低分子干渉核酸（ｓｉＮＡ）を用いた細胞内接着分子１（ＩＣＡＭ−１）遺伝子発現のＲＮＡ干渉媒介性阻害
WO2010111464A1 (en) 2009-03-27 2010-09-30 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF APOPTOSIS SIGNAL-REGULATING KINASE 1 (ASK1) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
WO2010111490A2 (en) 2009-03-27 2010-09-30 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF THE THYMIC STROMAL LYMPHOPOIETIN (TSLP) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
US20120004281A1 (en) 2009-03-27 2012-01-05 Merck Sharp & Dohme Corp RNA Interference Mediated Inhibition of the Nerve Growth Factor Beta Chain (NGFB) Gene Expression Using Short Interfering Nucleic Acid (siNA)
WO2011115817A1 (en) * 2010-03-16 2011-09-22 Isis Pharmaceuticals, Inc. Methods of preparing 2'-o-substituted purine nucleosides
CN102917585A (zh) 2010-04-01 2013-02-06 埃迪尼克斯医药公司 用于治疗病毒感染的化合物和药物组合物
US8518907B2 (en) 2010-08-02 2013-08-27 Merck Sharp & Dohme Corp. RNA interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (CTNNB1) gene expression using short interfering nucleic acid (siNA)
DK2606134T3 (da) 2010-08-17 2019-07-22 Sirna Therapeutics Inc RNA-Interferens-formidlet inhibering af hepatitis-B-virus (HBV)-genekspression ved hjælp af kort interfererende nukleinsyre (siNA)
WO2012027467A1 (en) 2010-08-26 2012-03-01 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF PROLYL HYDROXYLASE DOMAIN 2 (PHD2) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA)
DK2632472T3 (en) 2010-10-29 2018-03-19 Sirna Therapeutics Inc RNA INTERFERENCE-MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERRING NUCLEIC ACIDS (SINA)
WO2012154321A1 (en) 2011-03-31 2012-11-15 Idenix Pharmaceuticals, Inc. Compounds and pharmaceutical compositions for the treatment of viral infections
EP2755985B1 (en) 2011-09-12 2017-11-01 Idenix Pharmaceuticals LLC Compounds and pharmaceutical compositions for the treatment of viral infections
EP3358013B1 (en) 2012-05-02 2020-06-24 Sirna Therapeutics, Inc. Short interfering nucleic acid (sina) compositions
US9045521B2 (en) * 2012-07-31 2015-06-02 Ased, Llc Synthesis of deuterated ribo nucleosides N-protected phosphoramidites, and oligonucleotides
US9512162B2 (en) 2012-07-31 2016-12-06 Ased, Llc Synthesis of deuterated ribo nucleosides, N-protected phosphoramidites and oligonucleotides
CA2916533C (en) 2013-06-25 2022-12-20 University Of Canberra Methods and compositions for modulating cancer stem cells
SG11201601408PA (en) 2013-09-18 2016-04-28 Univ Canberra Stem cell modulation ii
JP2017528452A (ja) 2014-08-25 2017-09-28 ユニバーシティ・オブ・キャンベラＵｎｉｖｅｒｓｉｔｙ ｏｆ Ｃａｎｂｅｒｒａ がん幹細胞を調節するための組成物およびその使用
US10898505B2 (en) 2015-05-06 2021-01-26 Benitec Biopharma Limited Reagents for treatment of hepatitis B virus (HBV) infection and use thereof
AU2016269839B2 (en) 2015-06-03 2021-07-08 The University Of Queensland Mobilizing agents and uses therefor
US11273167B2 (en) 2015-08-03 2022-03-15 The Regents Of The University Of California Compositions and methods for modulating ABHD2 activity
JP2019508037A (ja) 2016-02-16 2019-03-28 イェール ユニバーシティーＹａｌｅ Ｕｎｉｖｅｒｓｉｔ 標的化遺伝子編集を増強するための組成物およびその使用方法
RU2755544C2 (ru) 2016-04-14 2021-09-17 Бенитек Биофарма Лимитед Реагенты для лечения окулофарингеальной мышечной дистрофии (OPMD) и их применение
WO2018057575A1 (en) 2016-09-21 2018-03-29 Alnylam Pharmaceuticals, Inc Myostatin irna compositions and methods of use thereof
EP3694867A1 (en) 2017-10-10 2020-08-19 Bristol-Myers Squibb Company Cyclic dinucleotides as anticancer agents
US20200282010A1 (en) 2017-11-08 2020-09-10 Epiaxis Therapeutics Pty Ltd Immunogenic compositions and uses therefor
CN112105625A (zh) 2018-03-07 2020-12-18 赛诺菲 核苷酸前体、核苷酸类似物以及含其的寡聚化合物
US20220372063A1 (en) 2019-09-05 2022-11-24 Sanofi Oligonucleotides containing nucleotide analogs
AU2020391116A1 (en) * 2019-11-27 2022-07-14 Alnylam Pharmaceuticals, Inc. Synthesis of 3'-RNA oligonucleotides
US20240092819A1 (en) 2020-10-20 2024-03-21 Sanofi Novel ligands for asialoglycoprotein receptor

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4987071A (en) 1986-12-03 1991-01-22 University Patents, Inc. RNA ribozyme polymerases, dephosphorylases, restriction endoribonucleases and methods
US6469158B1 (en) 1992-05-14 2002-10-22 Ribozyme Pharmaceuticals, Incorporated Synthesis, deprotection, analysis and purification of RNA and ribozymes
JPH0667492A (ja) 1992-08-24 1994-03-11 N T T Advance Tekunoroji Kk 像形成方法
EP0748382B1 (en) 1993-09-02 2002-11-06 Ribozyme Pharmaceuticals, Inc. Non-nucleotide containing enzymatic nucleic acid
DE69637256T2 (de) * 1996-01-16 2008-06-19 Sirna Therapeutics, Inc., Boulder Synthese von Methoxynukleoside und enzymatische Nukleisäure Moleküle
US5998203A (en) 1996-04-16 1999-12-07 Ribozyme Pharmaceuticals, Inc. Enzymatic nucleic acids containing 5'-and/or 3'-cap structures
US5962675A (en) 1996-02-13 1999-10-05 Ribozyme Pharmaceuticals, Inc. Chemical syntheses of 2'-O-methoxy purine nucleosides
US5849902A (en) 1996-09-26 1998-12-15 Oligos Etc. Inc. Three component chimeric antisense oligonucleotides
WO1998028317A2 (en) 1996-12-24 1998-07-02 Ribozyme Pharmaceuticals, Inc. Synthesis of nucleosides and polynucleotides
JP3032815B2 (ja) 1997-02-18 2000-04-17 工業技術院長 ２’−ｏ−シリル環状ケイ素化ヌクレオシド誘導体、その製造方法及びこれを用いた２’−ｏ−シリルヌクレオシドの製造方法
US6300483B1 (en) 1997-06-19 2001-10-09 Ribozyme Pharmaceuticals, Inc. Compositions inducing cleavage of RNA motifs
JP2002510207A (ja) 1997-06-19 2002-04-02 リボザイム・ファーマシューティカルズ・インコーポレーテッド 拡張された開裂ルールを有するハンマーヘッドリボザイム
AU750947C (en) 1997-09-22 2003-05-22 Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. Nucleic acid catalysts with endonuclease activity
WO1999055857A2 (en) 1998-04-29 1999-11-04 Ribozyme Pharmaceuticals, Inc. Nucleoside triphosphates and their incorporation into ribozymes

Also Published As

Publication number Publication date
ATE506372T1 (de) 2011-05-15
JP2004522695A (ja) 2004-07-29
DE60144479D1 (ja) 2011-06-01
US6686463B2 (en) 2004-02-03
AU8695901A (en) 2002-03-13
EP1313752A2 (en) 2003-05-28
WO2002018405A2 (en) 2002-03-07
US20020120129A1 (en) 2002-08-29
AU2001286959B2 (en) 2007-09-06
WO2002018405A3 (en) 2003-01-03
CA2421040A1 (en) 2002-03-07
EP1313752B1 (en) 2011-04-20

Similar Documents

Publication Publication Date Title
CA2421040C (en) Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives
AU2001286959A1 (en) Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives
US20020150936A1 (en) Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives
Mansuri et al. Preparation of 1-(2, 3-dideoxy-. beta.-D-glycero-pent-2-enofuranosyl) thymine (d4T) and 2', 3'-dideoxyadenosine (ddA): general methods for the synthesis of 2', 3'-olefinic and 2', 3'-dideoxy nucleoside analogs active against HIV
JP5677716B2 (ja) オリゴヌクレオチド類似体を含むキット及び方法並びにオリゴヌクレオチド類似体の使用
JP4151751B2 (ja) 新規ビシクロヌクレオシド類縁体
ES2516815T3 (es) Análogos de ácidos nucleicos bicíclicos modificados en la posición 6
US6090932A (en) Method of preparation of known and novel 2'-modified nucleosides by intramolecular nucleophilic displacement
JP3535519B2 (ja) Ｎ−２置換プリン類
HU211668A9 (en) Compounds and methods for inhibiting gene expression
JPH08225589A (ja) 修飾オリゴヌクレオチド、それらの製造、およびそれらの使用
Hunziker et al. Nucleic acid analogues: synthesis and properties
US5552539A (en) Process for the synthesis of ribonucleic acid (RNA) using a novel deprotection reagent
EP2006293B1 (en) 2'-hydroxyl-modified ribonucleoside derivative
US5674856A (en) Modified oligodeoxyribonucleoditides
Meher et al. Nucleobase Protection of Deoxyribo‐and Ribonucleosides
EP0799834A1 (en) Modified nucleotides
US20210238213A1 (en) SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING N6-(2-DEOXY-ALPHA,BETA-DERYTHROPENTOFURANOSYL)-2,6-DIAMINO-4-HYDROXY-5-FORMAMIDOPYRIMIDINE (Fapy.dG)
WO1995031470A2 (en) Antisense inhibitors of gene expression
CN101410406B (zh) 6-修饰的双环核酸类似物
US6509459B1 (en) Base protecting groups and rapid process for oligonucleotide synthesis
JP4255227B2 (ja) Ｎ３’−ｐ５’結合を有する２’，４’−ｂｎａオリゴヌクレオチド
CA2078256A1 (en) Synthesis of sulfide-linked di-or oligonucleotide analogs and incorporation into antisense dna or rna
RU2131436C1 (ru) Резистентные к нуклеазе олигонуклеозиды, способ их получения и резистентный к нуклеазе нуклеозидный димер
JPH0551599B2 (ja)

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20150831